US5021573A - Heterocyclic pigments and dyes - Google Patents
Heterocyclic pigments and dyes Download PDFInfo
- Publication number
- US5021573A US5021573A US07/340,348 US34034889A US5021573A US 5021573 A US5021573 A US 5021573A US 34034889 A US34034889 A US 34034889A US 5021573 A US5021573 A US 5021573A
- Authority
- US
- United States
- Prior art keywords
- group
- formula
- independently
- alkyl
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000049 pigment Substances 0.000 title description 15
- 239000000975 dye Substances 0.000 title description 2
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- -1 phenylaminocarbonyl Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 238000012986 modification Methods 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 101100177155 Arabidopsis thaliana HAC1 gene Proteins 0.000 claims 1
- 101100434170 Oryza sativa subsp. japonica ACR2.1 gene Proteins 0.000 claims 1
- 101100434171 Oryza sativa subsp. japonica ACR2.2 gene Proteins 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 description 16
- 239000004922 lacquer Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000000485 pigmenting effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VDBJCDWTNCKRTF-UHFFFAOYSA-N 6'-hydroxyspiro[2-benzofuran-3,9'-9ah-xanthene]-1,3'-dione Chemical compound O1C(=O)C2=CC=CC=C2C21C1C=CC(=O)C=C1OC1=CC(O)=CC=C21 VDBJCDWTNCKRTF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
- A61B17/04—Surgical instruments, devices or methods, e.g. tourniquets for suturing wounds; Holders or packages for needles or suture materials
- A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
- A61B17/06114—Packages or dispensers for needles or sutures
- A61B17/06133—Packages or dispensers for needles or sutures of parallelepipedal shape, e.g. made of rectangular or slightly oval panels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
- A61B17/04—Surgical instruments, devices or methods, e.g. tourniquets for suturing wounds; Holders or packages for needles or suture materials
- A61B17/06—Needles ; Sutures; Needle-suture combinations; Holders or packages for needles or suture materials
- A61B17/06114—Packages or dispensers for needles or sutures
- A61B2017/06142—Packages or dispensers for needles or sutures having needle- or suture- retaining members, e.g. holding tabs or needle parks
Definitions
- the invention relates primarily to pigments or solvent dyes, suitable for pigmenting or dyeing plastics in the mass.
- each R 1 independently is selected from oxygen, ⁇ NH or ⁇ N--R 2 where R 2 is an aromatic or heteroaromatic group, provided not more than two groups R 1 are selected from oxygen and ⁇ NH.
- R 2 is an aromatic group, it is a group of formula ⁇ or ⁇ ##STR3## where
- n 0, 1, 2 or 3 and
- each R 5 independently is selected from halogen, (C 1-4 alkyl)aminocarbonyl, (C 1-4 alkyl)carbonylamino, carboxyl, (C 1-4 alkoxy)carbonyl, phenlaminocarbonyl, benzoylamino or phenyloxycarbonyl or R 5 is a group of formula ⁇ ##STR4## where each R 10 independently is hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, cyan or nitro; provided not more than one group R 5 attached to any one phenyl group is a group of formula ⁇ .
- each R 10 is hydrogen.
- R 2 is a heteroaromatic group
- it is a thienyl, thiazolyl, pyrazolyl, imidazolyl, benzthiazolyl or benzimidazolyl group.
- R 1 is R 1 ' where each R 1 ' independently is selected from oxygen, ⁇ NH and ⁇ N--R 2 where R 2 is a group of formula ⁇ , provided that not more than two groups R 1 ' in the compound of formula I are selected from oxygen and ⁇ NH.
- R 1 is R 1 " where each group R 1 " independently is ⁇ N--R 2 ' where R 2 ' is a group of formula ⁇ ' ##STR5## where
- N' is 2 or 3;
- each R 5 ' independently is chloro, bromo, (C 1-4 alkyl)aminocarbonyl, (C 1-4 alkyl)carbonylamino, carboxyl, (C 1-4 alkoxy)carbonyl, phenylaminocarbonyl, benzoylamino, phenoxycarbonyl or a group of formula ⁇ ' ##STR6##
- R 1 is R 1 '" where each group R 1 '" independently is ⁇ N--R 2 " where R 2 " is a group of the formula ⁇ " ##STR7## where
- n' is 2 or 3;
- each R 5 independently is benzoylamino, chloro or bromo.
- R 1 '" is R 1 IV where each R 1 IV independently is ⁇ N--R 2 '" where R 2 '" is a group of formula ⁇ '", ⁇ IV and ⁇ V ##STR8## where each R 10 independently is selected from Br and Cl.
- R 2 '" are of formula ⁇ VI - ⁇ VIII ##STR9##
- Compounds of formula I can be prepared by reacting one mole of the compound of formula II ##STR10## with
- the compounds of formula II and III are known or may be made from known compounds by known methods.
- reaction of the compound of formula II with a compound of formula III can take place at an elevated temperature, preferably from 80°-120° C. according to known methods.
- the compounds of formula I are useful for dyeing in the mass plastics material.
- dyeing in the mass is meant dyeing in solvent-containing masses, dyeing in solvent free masses and dyeing in plastics resins, by known methods.
- Such processes include colouring oil based or water based paints or lacquers, spin dyeing from viscose or cellulose acetate, pigmenting of polyethylene, polystyrene, polyvinylchloride, rubber and artifical leather.
- the compounds of formula I can also be used for print dyeing of graphic fabrics, for dyeing paper masses, for coating textiles or for pigments printing.
- the dyeings especially the pigment dyeings, have good heat fastness, good light fastness, good weather fastness, good fastness to chemicals, good migration fastness, good fastness to blooming, good fastness to overcoating, good fastness to solvents.
- the dyeing strength is good and the compounds have good application properties, for instance good flocculation ability, good crystallinity and good dispersability.
- the pigment can be used as such without any further treatment for dyeing or pigmenting of plastics and lacquers.
- a reddish yellow colouring of the lacquer is produced with good fastness properties.
- the pigment may, instead of being used directly, be recrystallised in dimethylformamide and a ⁇ modification is formed having an X ray pattern significantly different to the ⁇ -form.
- the ⁇ modification can also be used to dye or pigment directly in plastics and lacquers.
- the X-ray data for the ⁇ -modification is: 5.6(w); 4.18(w); 3.99(w); 3.81(w); 3.57(w); 3.53(w); 3.45(w); 3.34(w); 3.22(w); 2.94(w).
- the X-ray data for the ⁇ -modification is: 10.6(w); 6.5(w); 6.2(w); 5.8(w); 4.4(w); 3.5(w); 3.35(w); 3.11(w).
- the resulting dispersion is sprayed on an aluminium piece, air dried for 30 minutes and stored for 30 minutes at 120° C.
- a brilliant yellow film results with good light and weathering fastnesses.
- the Application Example can be repeated using, instead of 4 g of ⁇ modification of Example, 4 g of any one of the products of Examples 2 to 10 or of the ⁇ modification of Example 1.
Landscapes
- Health & Medical Sciences (AREA)
- Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3813243 | 1988-04-20 | ||
| DE3813243 | 1988-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5021573A true US5021573A (en) | 1991-06-04 |
Family
ID=6352450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/340,348 Expired - Lifetime US5021573A (en) | 1988-04-20 | 1989-04-19 | Heterocyclic pigments and dyes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5021573A (ja) |
| JP (1) | JP2820238B2 (ja) |
| CH (1) | CH677927A5 (ja) |
| DE (1) | DE3911643C2 (ja) |
| FR (1) | FR2630453B1 (ja) |
| GB (1) | GB2217339B (ja) |
| HK (1) | HK79595A (ja) |
| IT (1) | IT1231756B (ja) |
| SG (1) | SG59888G (ja) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6540820B1 (en) | 1999-06-18 | 2003-04-01 | Clariant Finance (Bvi) Limited | Heterocyclic compounds |
| US20040063889A1 (en) * | 2001-02-21 | 2004-04-01 | Kaul Bansi Lal | Copolymer composition having pigment like properties |
| US20040060478A1 (en) * | 2001-02-10 | 2004-04-01 | Joachim Weber | Acid pigment dispersants and pigment preparations |
| US20060199882A1 (en) * | 2003-03-27 | 2006-09-07 | Heino Heckmann | Heterocyclic dyes based on benzodipyrroles |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2236629A1 (de) * | 1971-07-26 | 1973-02-08 | Nat Res Dev | Thermisch stabile benzobispyrrole |
| JPS4830656A (ja) * | 1971-08-26 | 1973-04-23 | ||
| JPS4928650A (ja) * | 1972-07-14 | 1974-03-14 | ||
| GB1561122A (en) * | 1977-05-04 | 1980-02-13 | Ford Motor Co | Organometallic polymers |
| US4255313A (en) * | 1979-04-20 | 1981-03-10 | Gulf Oil Corporation | Novel end-capped polyimide oligomers |
| US4289784A (en) * | 1978-10-23 | 1981-09-15 | Merck & Co., Inc. | Pyromellitic diimides and method of increasing feed efficiency in ruminant animals |
| GB1601267A (en) * | 1977-06-09 | 1981-10-28 | Ford Motor Co | Benzodipyrrole derivatives |
| US4320129A (en) * | 1979-02-05 | 1982-03-16 | Merck & Co., Inc. | Pyromellitic diimide complexes |
| JPH02108862A (ja) * | 1988-10-19 | 1990-04-20 | Hitachi Ltd | 内燃機関用点火装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH617450A5 (ja) * | 1975-09-26 | 1980-05-30 | Ciba Geigy Ag | |
| GB1568231A (en) * | 1976-03-10 | 1980-05-29 | Ici Ltd | Substituted 2,6-dioxo-2,6-dihydrobenzo (1:2-b; 4:5-6')-difuran or dipyrrole dyestuffs |
| EP0023080B1 (en) * | 1979-07-18 | 1983-07-27 | Imperial Chemical Industries Plc | Substituted 2,7-dioxo-2,7-dihydrobenzo(1:2-b; 5,6-b1)difuran or dipyrrole dyestuffs, processes for their preparation and their use for the colouration of aromatic polyester textile materials |
-
1989
- 1989-04-10 DE DE3911643A patent/DE3911643C2/de not_active Expired - Fee Related
- 1989-04-17 CH CH1448/89A patent/CH677927A5/de not_active IP Right Cessation
- 1989-04-18 FR FR8905244A patent/FR2630453B1/fr not_active Expired - Fee Related
- 1989-04-18 GB GB8908744A patent/GB2217339B/en not_active Expired - Lifetime
- 1989-04-18 SG SG1995906475A patent/SG59888G/en unknown
- 1989-04-19 IT IT8947863A patent/IT1231756B/it active
- 1989-04-19 JP JP1097672A patent/JP2820238B2/ja not_active Expired - Fee Related
- 1989-04-19 US US07/340,348 patent/US5021573A/en not_active Expired - Lifetime
-
1995
- 1995-05-25 HK HK79595A patent/HK79595A/xx not_active IP Right Cessation
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2236629A1 (de) * | 1971-07-26 | 1973-02-08 | Nat Res Dev | Thermisch stabile benzobispyrrole |
| JPS4830656A (ja) * | 1971-08-26 | 1973-04-23 | ||
| JPS4928650A (ja) * | 1972-07-14 | 1974-03-14 | ||
| GB1561122A (en) * | 1977-05-04 | 1980-02-13 | Ford Motor Co | Organometallic polymers |
| GB1601267A (en) * | 1977-06-09 | 1981-10-28 | Ford Motor Co | Benzodipyrrole derivatives |
| US4289784A (en) * | 1978-10-23 | 1981-09-15 | Merck & Co., Inc. | Pyromellitic diimides and method of increasing feed efficiency in ruminant animals |
| US4320129A (en) * | 1979-02-05 | 1982-03-16 | Merck & Co., Inc. | Pyromellitic diimide complexes |
| US4255313A (en) * | 1979-04-20 | 1981-03-10 | Gulf Oil Corporation | Novel end-capped polyimide oligomers |
| JPH02108862A (ja) * | 1988-10-19 | 1990-04-20 | Hitachi Ltd | 内燃機関用点火装置 |
Non-Patent Citations (9)
| Title |
|---|
| Chem. Abs., 100:192426w, (1984). * |
| Chem. Abs., 73:131375f, (1970). * |
| Chem. Abs., 88:145368c. * |
| Diebig et al., Chem. Abst., 80 3827n, (1974). * |
| Diebig et al., Chem. Abst., 80-3827n, (1974). |
| Hodd et al., Chem. Abst., 87 6400y, (1977). * |
| Hodd et al., Chem. Abst., 87-6400y, (1977). |
| Hodd, Chem. Abst., 78 137959z, (1973). * |
| Hodd, Chem. Abst., 78-137959z, (1973). |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6540820B1 (en) | 1999-06-18 | 2003-04-01 | Clariant Finance (Bvi) Limited | Heterocyclic compounds |
| US20040060478A1 (en) * | 2001-02-10 | 2004-04-01 | Joachim Weber | Acid pigment dispersants and pigment preparations |
| US6918958B2 (en) | 2001-02-10 | 2005-07-19 | Clariant Gmbh | Acid pigment dispersants and pigment preparations |
| US20040063889A1 (en) * | 2001-02-21 | 2004-04-01 | Kaul Bansi Lal | Copolymer composition having pigment like properties |
| US7087677B2 (en) | 2001-02-21 | 2006-08-08 | Mitchell A. Winnik | Copolymer composition having pigment like properties |
| US20060199882A1 (en) * | 2003-03-27 | 2006-09-07 | Heino Heckmann | Heterocyclic dyes based on benzodipyrroles |
Also Published As
| Publication number | Publication date |
|---|---|
| CH677927A5 (ja) | 1991-07-15 |
| IT1231756B (it) | 1991-12-21 |
| GB8908744D0 (en) | 1989-06-07 |
| JP2820238B2 (ja) | 1998-11-05 |
| DE3911643A1 (de) | 1989-11-02 |
| JPH0211663A (ja) | 1990-01-16 |
| HK79595A (en) | 1995-06-01 |
| FR2630453B1 (fr) | 1994-04-01 |
| SG59888G (en) | 1995-09-01 |
| GB2217339A (en) | 1989-10-25 |
| GB2217339B (en) | 1992-08-12 |
| DE3911643C2 (de) | 1999-09-23 |
| FR2630453A1 (fr) | 1989-10-27 |
| IT8947863A0 (it) | 1989-04-19 |
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